Water → HCID 14884002, compound

HRID 483905Notes

Reaction equation

HRID 483905 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=O)=[CH:14][CH:13]=1)=[O:11].[CH2:22]([NH2:25])[CH2:23][CH3:24].O>O1CCCC1>[CH2:22]([NH:25][C:19](=[O:21])[CH2:18][C:15]1[CH:14]=[CH:13][C:12]([C:10](=[O:11])[NH:9][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=2[Cl:1])=[CH:17][CH:16]=1)[CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 7852PropylamineHCID 14883993HCID 14883993, compound

Product 1

HCID 14884002HCID 14884002, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 g of 4-(2,3-dichlorophenylcarbamoyl)phenyl acetic acid was dissolved in 30 ml of anhydrous tetrahydrofuran. While cooling the solution with ice water, 0.75 g of N,N'-carbonyldiimidazole was added thereto, and the mixture was stirred for 30 minutes. Thereafter, 0.27 g of n-propylamine was added thereto. The mixture was returned to room temperature and stirred for 5 hours. After completion of the reaction, the reaction solution was poured into 200 ml of water. The resulting crystals were collected by filtration, washed with water and dried, and then recrystallized from benzene-hexane to obtain 1.5 g of desired N-n-propyl-4-(2,3-dichlorophenylcarbamoyl)phenylacetamide. The yield was 88.8%, and the melting point of this compound was from 177° to 178° C.

Workup

  1. additionwas added
  2. customwas returned to room temperature
  3. stirringstirred for 5 hours
  4. customAfter completion of the reaction
  5. filtrationThe resulting crystals were collected by filtration
  6. washwashed with water
  7. customdried
  8. customrecrystallized from benzene-hexane

Sources & evidence

ORD record
ord-89fd3472483e4647a6d6447d95d3ce60
Source dataset
uspto-grants-1993_07
Patent number
US05227511

Reaction notes

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